6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Base Information

Chemical Name:6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate
CAS No.:1394857-58-9
Molecular Formula:C₃₃H₃₉N₃O₁₄
Molecular Weight:701.684
Hs Code.:

Synonyms:6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

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Chemical Property of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

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Technology Process of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

There total 13 articles about 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 1394857-46-5
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

: 1394857-58-9
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 2.5h;
DOI:10.1021/jo300722y

Reference yield:

: 2-azido-2-deoxy-D-glucose

: 1394857-58-9
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: Multi-step reaction with 11 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Cooling with ice

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Inert atmosphere

3: methanol; sodium / 1.5 h / Inert atmosphere

4: camphorsulfonic acid / acetonitrile / 16 h

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

6: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

7: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °C

8: N-Bromosuccinimide / acetone / 0 °C

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / Inert atmosphere

10: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -25 °C / Molecular sieve; Inert atmosphere

11: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2.5 h

With pyridine; methanol; dmap; N-Bromosuccinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; water; sodium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;
DOI:10.1021/jo300722y

Reference yield:

: 183875-35-6
phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside

: 1394857-58-9
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: Multi-step reaction with 7 steps

1: methanol; sodium / 1.5 h / Inert atmosphere

2: camphorsulfonic acid / acetonitrile / 16 h

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

4: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

5: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °C

6: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.25 h / Molecular sieve

7: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2.5 h

With pyridine; methanol; dmap; N-iodo-succinimide; borane-THF; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; water; silver trifluoromethanesulfonate; sodium; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y